In a mild and rapid method for the iodination of arenes, silver(I) triflimide is
used as a catalyst for activation of N-iodosuccinimide. The is suitable
for a wide range of anisoles, anilines, acetanilides, and phenol derivatives and
allowed the late-stage iodination of biologically active compounds.
D. T. Racys, S. A. I. Sharif, S. L. Pimlott, A. Sutherland, J. Org. Chem.,
2016,
81, 772-780.

The use of a hexafluoroisopropanol as solvent enables a mild and regioselective
halogenation of a broad range of arenes and heterocycles with N-halosuccinimides
in good yields. In addition, the versatility of the method is demonstrated by
the development of one-pot sequential dihalogenation and halogenation-Suzuki
cross-coupling reactions.
R.-J. Tang, T. Milcent, B. Crousse, J. Org. Chem.,
2018, 83, 930-938.

Aryl and heteroaryl boronic acids react with N-iodosuccinimide and
N-bromosuccinimide to give the corresponding iodo- and bromo-arenes in good
to excellent yields. The reaction is usually highly regioselective and yields
only the ipso-substituted product.
C. Thiebes, G. K. Surya Prakash, N. A. Petasis, G. A. Olah, Synlett,
1998, 141-142.

Using cyano as the directing group, a palladium-catalyzed ortho-halogenation
(I, Br, Cl) reaction gave good to excellent yields. The method is compatible to
arylnitriles with either electron-withdrawing or electron-donating groups. The
present method was successfully applied to the synthesis of the precursors of
paucifloral F and isopaucifloral F.
B. Du, X. Jiang, P. Sun, J. Org. Chem., 2013,
78, 2786-2791.

Trapping of a diazo species in an intermolecular fashion by two independent ion
species in tandem at the carbene center installs an electrophile and a
nucleophile on the same carbon. This metal-free concept enables regioselective
syntheses of various vinyl halides, vinyl sulfones, and alkyne derivatives.
D. P. Ojha, K. R. Prabhu, Org. Lett.,
2015,
17, 18-21.

Using triethylamine as catalyst in Hunsdiecker reactions with N-halosuccinimides
as Br+ or I+ source, cinnamic acids, and propiolic acids are
converted to the corresponding α-halostyrenes and 1-halo-1-alkynes in good isolated yields within 1-5 min.
J. Prakash, S. Roy, J. Org. Chem.,
2002, 67, 7861-7864.

A sequence consisting of an electrophilic cyclization in the presence of N-iodosuccinimide
(NIS) and an 1,2-migration allows the construction of 4-iodo-3-furanones from
2-alkynyl-2-silyloxy carbonyl compounds. In a more versatile variant, AuCl3
catalyzes the tandem reaction in the presence of NIS to provide highly
substituted heterocycles in good yields.
B. Crone, S. F. Kirsch, J. Org. Chem., 2007,
72, 5435-5438.

Various tert-butyldimethylsilyl ethers are easily removed in excellent
yields by treatment with a catalytic amount of N-iodosuccinimide in
methanol. This method allows a selective deprotection of TBDMS ethers of
alcohols in the presence of TBDMS ethers of phenols.
B. Karimi, A. Zamani, D. Zarayee, Tetrahedron Lett., 2004,
45, 9139-9141.

Use of La(OTf)3 as a Lewis acid promoter for N-iodosuccinimide-mediated
activation of thioglycosides enables a smooth glycosylation reaction with good
to excellent yields and stereoselectivity.
S. Mukherjee, B. Mukhopadhyay, Synlett, 2010,
2853-2856.

Highly substituted oxazoles can be synthesized from readily accessible ynamides
in the presence of ytterbium(III) trifluoromethanesulfonate, N-iodosuccinimide,
and acetonitrile. Hydroamidation and iodo-imidation of ynamides to ketene
aminals are also demonstrated. The reactions are scalable to the gram scale,
testifying the robustness of the transformations.

A rapid synthesis of indoles from N-Ts-2-alkenylanilines involves a
NIS-mediated cascade C-N bond formation/aromatization. A series of indoles with
various functional groups have been synthesized in very good yields under mild
conditions without any other additives or catalysts.
Y.-L. Li, J. Li, A.-L. Ma, Y.-N. Huang, J. Deng, J. Org. Chem.,
2015,
80, 3841-3851.

Gold(I)-catalyzed cycloisomerization of 1-(2-(tosylamino)phenyl)prop-2-yn-1-ols
enables the preparation of 1H-indole-2-carbaldehydes and (E)-2-(iodomethylene)indolin-3-ols
in the presence of N-iodosuccinimide (NIS). The reactions were shown to
be operationally simplistic and proceed efficiently for a wide variety of
substrates, affording the corresponding products in very good yields.
P. Kothandaraman, S. R. Mothe, S. S. M. Toh, P. W. H. Chan, J. Org. Chem., 2011,
76, 7633-7640.

Treatment of N-tosyl-2-propynylamines with diphenyliodonium triflate in
the presence of K3PO4 and a catalytic amount of CuCl at
room temperature followed by N-iodosuccinimide and BF3·OEt2
at 0°C, and then NaOH in methanol solution provided 3-iodo-4-arylquinolines.
Products underwent various cross-coupling reactions and were smoothly
dehalogenated with zinc.
T. Sasaki, K. Moriyama, H. Togo, J. Org. Chem.,
2017, 82, 11727-11734.

The intramolecular cyclization of 1-azido-2-(2-propynyl)benzene proceeds
smoothly in the presence of electrophilic reagents in CH3NO2
at room temperature or in the presence of catalytic amounts of AuCl3/AgNTf2
in THF at 100°C to afford the corresponding quinolines 2 in good to high yields.
Z. Huo, I. D. Gridnev, Y. Yamamoto, J. Org. Chem., 2010,
75, 1266-1270.

A convenient radical oxidative cyclization mediated by N-iodosuccinimide
(NIS) enables the synthesis of a series of dibenzopyranones from a wide scope of
2-arylbenzoic acids. The methodology offers good functional group tolerance and
mild reaction conditions without the use of transition metals.
P. Gao, Y. Wei, Synthesis, 2014, 46,
343-347.